Acetonitrile → HCID 136337207, compound

HRID 1891219Notes

Reaction equation

HRID 1891219 reaction equation
C([C:3]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH2:11])[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](Cl)[N:13]=2)[N:4]=1)C.[OH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[C:35](#N)[CH3:36]>>[NH2:11][C:6]1[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[OH:19])[N:13]=2)[N:4]=[CH:3][C:7]=1[C:8]([O:10][CH2:35][CH3:36])=[O:9]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 2773454(2-Hydroxyphenyl)boronic acidHCID 86644573HCID 86644573, compound

Product 1

HCID 136337207HCID 136337207, compound

Conditions

Temperature
85 °C

Procedure

To a vial containing the title compound from Example 10 Step A (200 mg, 0.75 mmol) were added 2-hydroxyphenylboronic acid (125 g, 0.90 mmol) and trans-dichlorobis(triphenylphosphine) palladium (II) (53 mg, 0.075 mmol). Acetonitrile (4 mL) and sodium carbonate (1.9 mL, 1.0 M aqueous, 1.9 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction vial was capped and the reaction mixture was stirred at 85° C. After 18 h, the reaction mixture was allowed to cool to room temperature and was poured into water. The mixture was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 75% EtOAc in hexanes, then 75 to 100% EtOAc) provided the title compound: LCMS m/z 324.9 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 10.69 (s, 1H), 8.02 (t, J=8.0 Hz, 1H), 7.85 (dd, J=8.0, 3.5 Hz, 1H), 7.83 (s, 1H), 7.72-7.68 (m, 2H), 7.39-7.35 (m, 1H), 7.07-7.05 (m, 1H), 7.02-6.99 (m, 1H), 6.63 (br s, 2H), 4.32 (q, J=7.0 Hz, 2H), 1.37 (t, J=7.0 Hz, 3H).

Workup

  1. customthe resulting mixture was degassed via nitrogen
  2. customsparge
  3. customThe reaction vial was capped
  4. temperatureto cool to room temperature
  5. additionwas poured into water
  6. extractionThe mixture was extracted with EtOAc
  7. concentrationthe organic phase was concentrated in vacuo
  8. customPurification by chromatography on silica gel (0 to 75% EtOAc in hexanes

Sources & evidence

ORD record
ord-2782587ea9b741bd9cbb2f7050514810
Source dataset
uspto-grants-2013_08
Patent number
US08507512B2

Reaction notes

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